2-Chloro-6-methylbenzothiazole synthesis
- Product Name:2-Chloro-6-methylbenzothiazole
- CAS Number:3507-26-4
- Molecular formula:C8H6ClNS
- Molecular Weight:183.66
2536-91-6
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Yield: 74%
Reaction Conditions:
with tert.-butylnitrite;copper dichloride in acetonitrile at 20;
Steps:
1.AA
t-Butyl nitrite (3.25 mL, 27.4 mmol) was added to a suspension of copper (II) chloride (2.95 g, 22.0 mmol) in CH3CN (31 mL). 6-Methyl-2- aminobenzothazole (3.0 g, 18 mmol) was added portionwise over ~30 min., and the reaction mixture was stirred at rt overnight. The reaction mixture was poured into 20% aqueous HCl (100 mL) and was extracted with EtOAc (3 x). The combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was purified by column chromatography (0 to10% EtOAc in Hexanes gradient), yielding 2.50 g (74%) of the title compound as a yellowish oil that solidified on standing. LC-MS: RT = 9.71 min., [M+H]+ = 184.0.
References:
CRITICAL THERAPEUTICS, INC. WO2007/146066, 2007, A2 Location in patent:Page/Page column 93
2268-79-3
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20174-69-0
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